fondaparinux Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
synthetic heparinoids 1236 104993-28-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fondaparinux
  • fondaparin
  • heparin pentasaccharide
  • fondaparinux sodium
  • arixtra
  • fondaparin sodium
Synthetic pentasaccharide that mediates the interaction of HEPARIN with ANTITHROMBINS and inhibits FACTOR Xa; it is used for prevention of VENOUS THROMBOEMBOLISM after surgery.
  • Molecular weight: 1508.22
  • Formula: C31H53N3O49S8
  • CLOGP: -10.96
  • LIPINSKI: 3
  • HAC: 52
  • HDO: 19
  • TPSA: 805.48
  • ALOGS: -2.28
  • ROTB: 27

Drug dosage:

DoseUnitRoute
2.50 mg P

ADMET properties:

PropertyValueReference
CL (Clearance) 0.07 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.21 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 19.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 7, 2001 FDA MYLAN IRELAND LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Haematoma 1067.24 53.59 210 1501 4911 2351463
Anaemia 612.97 53.59 197 1514 34595 2321779
Muscle haemorrhage 514.12 53.59 83 1628 556 2355818
Haemoglobin decreased 414.64 53.59 126 1585 18025 2338349
Pulmonary embolism 372.36 53.59 116 1595 17967 2338407
Shock haemorrhagic 310.03 53.59 60 1651 1223 2355151
Post procedural haemorrhage 301.78 53.59 59 1652 1270 2355104
Incorrect product administration duration 286.87 53.59 63 1648 2432 2353942
Cerebral haemorrhage 280.94 53.59 72 1639 5432 2350942
Haemorrhage 274.26 53.59 82 1629 10957 2345417
Melaena 265.81 53.59 65 1646 4041 2352333
Haematemesis 220.89 53.59 56 1655 4026 2352348
Post procedural haematoma 217.32 53.59 36 1675 284 2356090
Heparin-induced thrombocytopenia 215.38 53.59 42 1669 887 2355487
Deep vein thrombosis 204.02 53.59 68 1643 12864 2343510
Subdural haematoma 183.69 53.59 43 1668 2203 2354171
Off label use 178.84 53.59 103 1608 73495 2282879
Retroperitoneal haematoma 157.85 53.59 29 1682 437 2355937
Blood loss anaemia 143.02 53.59 31 1680 1114 2355260
Intra-abdominal haematoma 135.45 53.59 24 1687 291 2356083
Abdominal wall haematoma 125.26 53.59 24 1687 458 2355916
Red blood cell count decreased 124.46 53.59 36 1675 4230 2352144
Thrombocytopenia 122.36 53.59 52 1659 19079 2337295
Gastrointestinal haemorrhage 121.91 53.59 46 1665 12389 2343985
Incision site haematoma 121.66 53.59 17 1694 32 2356342
Subcutaneous haematoma 114.92 53.59 21 1690 306 2356068
Haematocrit decreased 110.83 53.59 33 1678 4285 2352089
Abdominal pain 110.19 53.59 58 1653 34316 2322058
Haemorrhage subcutaneous 106.54 53.59 22 1689 622 2355752
Compartment syndrome 91.22 53.59 18 1693 402 2355972
Thrombosis 90.16 53.59 34 1677 9110 2347264
Platelet count increased 88.59 53.59 24 1687 2213 2354161
Shock 87.30 53.59 27 1684 3977 2352397
Rectal haemorrhage 81.08 53.59 28 1683 5828 2350546
Hepatic function abnormal 80.00 53.59 28 1683 6064 2350310
Skin necrosis 78.56 53.59 19 1692 1112 2355262
Intra-abdominal haemorrhage 76.64 53.59 16 1695 477 2355897
Dyspnoea 72.58 53.59 61 1650 78672 2277702
Pallor 72.24 53.59 23 1688 3719 2352655
Thrombocytosis 71.77 53.59 17 1694 910 2355464
Incision site haemorrhage 68.19 53.59 12 1699 139 2356235
Oedema peripheral 67.29 53.59 37 1674 23726 2332648
Coma 65.76 53.59 27 1684 9029 2347345
Hemiplegia 64.74 53.59 17 1694 1388 2354986
Pain in extremity 63.50 53.59 44 1667 42496 2313878
Brain herniation 62.75 53.59 14 1697 573 2355801
Cerebral haematoma 62.75 53.59 14 1697 573 2355801
Post procedural swelling 60.28 53.59 10 1701 79 2356295
Hypotension 59.10 53.59 38 1673 32398 2323976
Wound complication 58.05 53.59 12 1699 340 2356034
Renal failure 57.46 53.59 30 1681 17319 2339055
Platelet count decreased 57.15 53.59 29 1682 15784 2340590
Peritoneal haemorrhage 55.46 53.59 12 1699 425 2355949
Injection site haematoma 55.34 53.59 16 1695 1866 2354508

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Haematoma 361.05 46.92 84 1065 3861 1741771
Anaemia 344.10 46.92 126 1023 29331 1716301
Incorrect product administration duration 322.30 46.92 61 1088 994 1744638
Cerebral haemorrhage 209.55 46.92 60 1089 6217 1739415
Muscle haemorrhage 203.41 46.92 40 1109 796 1744836
Haemorrhage 199.39 46.92 64 1085 9765 1735867
Haemoglobin decreased 157.56 46.92 62 1087 17052 1728580
Melaena 156.76 46.92 46 1103 5164 1740468
Post procedural haemorrhage 154.52 46.92 35 1114 1395 1744237
Pulmonary embolism 151.36 46.92 56 1093 13003 1732629
Shock haemorrhagic 144.05 46.92 33 1116 1383 1744249
Haematemesis 142.03 46.92 41 1108 4336 1741296
Heparin-induced thrombocytopenia 135.10 46.92 30 1119 1089 1744543
Off label use 134.61 46.92 71 1078 38500 1707132
Gastrointestinal haemorrhage 114.81 46.92 47 1102 14220 1731412
Post procedural haematoma 113.63 46.92 21 1128 293 1745339
Thrombocytopenia 109.13 46.92 51 1098 21198 1724434
Deep vein thrombosis 101.83 46.92 39 1110 9881 1735751
Subdural haematoma 97.15 46.92 29 1120 3428 1742204
Haematuria 93.16 46.92 34 1115 7526 1738106
Thrombosis 71.49 46.92 28 1121 7493 1738139
Retroperitoneal haematoma 65.06 46.92 14 1135 435 1745197
Retroperitoneal haemorrhage 63.42 46.92 14 1135 491 1745141
Pain in extremity 61.14 46.92 33 1116 18439 1727193
Intra-abdominal haematoma 60.49 46.92 12 1137 247 1745385
Thrombocytosis 60.27 46.92 14 1135 619 1745013
Adrenal haemorrhage 59.25 46.92 10 1139 79 1745553
Gastric haemorrhage 54.41 46.92 18 1131 2960 1742672
Drug ineffective 51.65 46.92 48 1101 63753 1681879
Haemarthrosis 49.38 46.92 12 1137 644 1744988
Gastric ulcer haemorrhage 49.11 46.92 13 1136 986 1744646
Acute kidney injury 48.52 46.92 36 1113 34908 1710724
Pallor 48.16 46.92 17 1132 3394 1742238

Pharmacologic Action:

SourceCodeDescription
ATC B01AX05 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Other antithrombotic agents
FDA EPC N0000175637 Factor Xa Inhibitor
MeSH PA D000925 Anticoagulants
MeSH PA D000991 Antithrombins
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D065427 Factor Xa Inhibitors
MeSH PA D006401 Hematologic Agents
MeSH PA D011480 Protease Inhibitors
MeSH PA D015842 Serine Proteinase Inhibitors
CHEBI has role CHEBI:50249 anticoagulant

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Deep venous thrombosis indication 128053003
Pulmonary thromboembolism indication 233935004
Prevention of deep vein thrombosis indication 439993001
Myocardial infarction off-label use 22298006 DOID:5844
Acute coronary syndrome off-label use 394659003
Diabetic retinopathy contraindication 4855003 DOID:8947
Gastrointestinal ulcer contraindication 40845000
Acute nephropathy contraindication 58574008
Blood coagulation disorder contraindication 64779008 DOID:1247
Operation on brain contraindication 70586009
Heparin-induced thrombocytopenia contraindication 73397007
Kidney disease contraindication 90708001 DOID:557
Autoimmune thrombocytopenia contraindication 128091003
Hemorrhagic cerebral infarction contraindication 230706003
Local anesthetic intrathecal block contraindication 231249005
Procedure on spine contraindication 238181003
Anemia contraindication 271737000 DOID:2355
Lumbar puncture contraindication 277762005
Bacterial endocarditis contraindication 301183007
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Surgical procedure on eye proper contraindication 373353005
Hypertensive urgency contraindication 443482000
Significant Bleeding contraindication
Platelet Aggregation Inhibition contraindication
Placement of Epidural Catheter contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 0.23 acidic
pKa2 0.94 acidic
pKa3 2.46 acidic
pKa4 3.08 acidic
pKa5 11.49 acidic
pKa6 11.98 acidic
pKa7 12.26 acidic
pKa8 12.43 acidic
pKa9 12.91 acidic
pKa10 13.69 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Antithrombin-III Secreted ACTIVATOR Kd 7.49 IUPHAR CHEMBL

External reference:

IDSource
D000077425 MESH_DESCRIPTOR_UI
4021296 VUID
N0000148733 NUI
C1098510 UMLSCUI
D01844 KEGG_DRUG
395236007 SNOMEDCT_US
d04786 MMSL
16268 MMSL
321208 RXNORM
4021296 VANDF
009549 NDDF
708189008 SNOMEDCT_US
C049714 MESH_SUPPLEMENTAL_RECORD_UI
DB00569 DRUGBANK_ID
CHEMBL1200644 ChEMBL_ID
J177FOW5JL UNII
NTO PDB_CHEM_ID
NTP PDB_CHEM_ID
CHEBI:61033 CHEBI
7653 INN_ID
114870-03-0 SECONDARY_CAS_RN
CHEMBL1201202 ChEMBL_ID
CHEMBL1276258 ChEMBL_ID
5282448 PUBCHEM_CID
6819 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3443 INJECTION 2.50 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3454 INJECTION 5 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3465 INJECTION 7.50 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3476 INJECTION 10 mg SUBCUTANEOUS ANDA 18 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-154 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS ANDA 18 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-155 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 18 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-156 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS ANDA 18 sections
fondaparinux sodium HUMAN PRESCRIPTION DRUG LABEL 1 11797-157 INJECTION, SOLUTION 10 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-606 INJECTION 10 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-607 INJECTION 2.50 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-608 INJECTION 5 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 43598-609 INJECTION 7.50 mg SUBCUTANEOUS ANDA 18 sections
ARIXTRA HUMAN PRESCRIPTION DRUG LABEL 1 54868-5501 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS NDA 19 sections
ARIXTRA HUMAN PRESCRIPTION DRUG LABEL 1 54868-5652 INJECTION, SOLUTION 5 mg SUBCUTANEOUS NDA 19 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-678 INJECTION 2.50 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-679 INJECTION 5 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-680 INJECTION 7.50 mg SUBCUTANEOUS ANDA 18 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 55111-681 INJECTION 10 mg SUBCUTANEOUS ANDA 18 sections
FONDAPARINUX SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 55150-230 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS ANDA 19 sections
FONDAPARINUX SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 55150-231 INJECTION, SOLUTION 5 mg SUBCUTANEOUS ANDA 19 sections
FONDAPARINUX SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 55150-232 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS ANDA 19 sections
FONDAPARINUX SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 55150-233 INJECTION, SOLUTION 10 mg SUBCUTANEOUS ANDA 19 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-582 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS NDA authorized generic 19 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-583 INJECTION, SOLUTION 5 mg SUBCUTANEOUS NDA authorized generic 19 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-584 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS NDA authorized generic 19 sections
Fondaparinux Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-585 INJECTION, SOLUTION 10 mg SUBCUTANEOUS NDA authorized generic 19 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-592 INJECTION, SOLUTION 2.50 mg SUBCUTANEOUS NDA 18 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-593 INJECTION, SOLUTION 5 mg SUBCUTANEOUS NDA 18 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-594 INJECTION, SOLUTION 7.50 mg SUBCUTANEOUS NDA 18 sections
Arixtra HUMAN PRESCRIPTION DRUG LABEL 1 67457-595 INJECTION, SOLUTION 10 mg SUBCUTANEOUS NDA 18 sections